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Benzofuryl-containing 1, 3, 4-oxadiazole compound

A technology based on benzofuryl and oxadiazoles, which is applied in the fields of organic chemistry and acaricides, can solve the problems of many residues, the preparation method is not environmentally friendly, and the insecticidal activity of oxadiazoles has not been reported, so as to achieve the utilization of atoms high rate effect

Active Publication Date: 2018-10-23
湖南博隽生物医药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxymethyl)-5-(4-methoxyphenyl)-[1,3,4 ]oxadiazole and 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxymethyl)-5-(2-chlorophenyl)-[1,3 ,4] The insecticidal activity of oxadiazole has not been reported
According to the 1,3,4-oxadiazole compounds that have been reported above, either the insecticidal activity needs to be improved, or there are many residues, or the preparation method is not environmentally friendly, and the atom utilization rate is not high

Method used

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  • Benzofuryl-containing 1, 3, 4-oxadiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetylhydrazide

[0031] Put 1.64g (0.10mol) of furanol and 80mL of anhydrous acetone in a reaction flask, add 27.6g (0.20mol) of potassium carbonate, stir for 0.5h, add 2.45g (0.20mol) of ethyl chloroacetate, reflux for 4.0h, cool , remove acetone by precipitation, add 60mL hydrazine hydrate to the residue, heat up to reflux, react for 2.0h, cool, remove part of hydrazine hydrate under reduced pressure, leave still to precipitate a white solid, suction filter, recrystallize from ethanol to obtain a white powder 2-(( 2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetylhydrazide, yield 82.0%.

[0032] (2) Dissolve 1mmol 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetylhydrazide in 30ml ethanol, and add 1mmmol 4-methanol in batches under stirring Oxybenzaldehyde and 0.1mmol acetic acid were heated to reflux, reacted for 2.0h, and a white solid was precipitated after cooling, and N-(4-methoxyphenyl)-2-(...

Embodiment 2

[0036] (1) Preparation of 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetylhydrazide

[0037] Put 1.75g ​​(0.10mol) of furanol and 82mL of anhydrous acetone in a reaction flask, add 28.6g (0.20mol) of potassium carbonate, stir for 0.5h, add 2.64g (0.20mol) of ethyl chloroacetate, reflux for 4.0h, cool , remove acetone by precipitation, add 65mL hydrazine hydrate to the residue, heat up to reflux, react for 2.0h, cool down, remove part of hydrazine hydrate under reduced pressure, leave still to precipitate a white solid, filter with suction, and recrystallize from ethanol to obtain a white powder 2-(( 2,2-Dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetohydrazide, yield 84.0%.

[0038] (2) Dissolve 1mmol 2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetylhydrazide in 30ml ethanol, add 1mmol 2-chloro Benzaldehyde and 0.1mmol acetic acid were heated to reflux, reacted for 2.0h, and a white solid was precipitated after cooling, and N-(2-chlorophenyl)-2-((2,2-dimethyl-2,3- Di...

experiment example

[0042] Determination of Acaricidal Activity of a 1,3,4-Oxadiazole Compound Containing Benzofuryl

[0043] Referring to the "National Southern Pesticide Creation Center Bioassay Standard Procedure", accurately weigh (accurate to 0.0001g) a certain mass of target compound, add N,N-dimethylformamide (DMF) containing 0.1% Tween-80, and prepare The mother solution with a compound mass fraction of 5% was diluted with distilled water to form a 600mg / L mass concentration of the drug solution. DMF was used as the blank control. The acaricidal activity of the target compounds against Tetranychus cinnabarinus was tested by living pot method.

[0044] After sowing broad beans in small pots (diameter 5 cm), when the seedlings were about 5-8 cm high, each seedling was inoculated with quantitative adult mites (20 heads); into the spray tower, sprayed with prepared different concentrations of liquid medicine and DMF respectively. Observe for 5 to 10 days, investigate the number of live inse...

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Abstract

The invention discloses a benzofuryl-containing 1, 3, 4-oxadiazole compound. A preparation method of the benzofuryl-containing 1, 3, 4-oxadiazole compound comprises that 1) 2-((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl)oxo)acethydrazide respectively reacts with 4-methoxybenzaldehyde and 2-chlorobenzaldehyde in an organic solvent I under catalyst conditions to produce an intermediate 2-((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl)oxo)acetyl hydrazone, and 2) the intermediate 2-((2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl)oxo)acetyl hydrazone reacts in an organic solvent II under iodobenzene diacetate conditions to produce a desired compound (I) or (II). The compound has good insecticidal activity and good inhibitory activity to Tetranychus cinnabarinus at a test concentration. The preparationmethod is easy to operate, has a high yield and provides the candidate drug for the creation of the acaricide compound.

Description

technical field [0001] The present invention relates to a class of novel compounds and applications thereof, in particular to a benzofuryl-containing 1,3,4-oxadiazole compound, a preparation method thereof, and an application in the preparation of acaricides. Background technique [0002] Acarids are a class of common pests that harm vegetables, fruit trees, cotton and other crops, and often cause devastating disasters to crops. Herbivorous mites have the characteristics of small size, fast reproduction, strong adaptability and easy resistance to pesticides, and are recognized as difficult-to-control harmful biological communities. Therefore, it is of great significance to develop acaricides with high efficiency, low toxicity, low residue and different action mechanisms. [0003] 1,3,4-oxadiazole (1,3,4-oxazdiazole) is a five-membered heterocyclic ring containing O and N atoms, which has a wide range of pharmaceutical and pesticide activities. With the in-depth research on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12A01P7/02
CPCC07D413/12
Inventor 李丽娟朱露晶万迎春
Owner 湖南博隽生物医药有限公司
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